Addition and condensation polymers prepared from halogenated reactants

Patent metadata

Field	Value
Publication number	US-2020299451-A1
Application number	US-201816651397-A
Country	US
Kind code	A1
Filing date	Sep 25, 2018
Priority date	Sep 27, 2017
Publication date	Sep 24, 2020
Grant date	—

Abstract

Polymers containing halogen functionality are prepared by the addition or condensation polymerization of at least one halogenated reactant containing at least two active hydrogen-containing functional groups per molecule and at least one halogenated heteroalkyl or halogenated heteroalkenyl group per molecule and at least one co-reactant containing at least two functional groups reactive with the active hydrogen groups of the at least one halogenated reactant.

First claim

1 . A polymer which is an addition or condensation polymerization product of reactants comprising:
a) at least one halogenated reactant comprising at least two active hydrogen-containing functional groups and at least one halogenated heteroalkyl or halogenated heteroalkenyl group; and b) at least one co-reactant comprising at least two functional groups reactive with the active hydrogen-containing functional groups of the at least one halogenated reactant.

2 . The polymer of claim 1 , wherein the at least one co-reactant comprises at least two functional groups selected from the group consisting of isocyanate groups, epoxy groups, carboxylic acid groups, carboxylate groups, anhydride groups, and acyl halide groups.

3 . The polymer of claim 1 , wherein the polymer is a polyamide, polyester, polyurea, polyurethane or epoxy polymer.

4 . The polymer of claim 1 , wherein the at least one halogenated reactant comprises at least two active hydrogen-containing functional groups and at least one halogenated heteroalkyl group corresponding to formula (I):
CX 1 X 2 HCX 3 X 4 —Y—  (I)
wherein X 1 , X 2 , X 3 and X 4 are independently selected from a hydrogen atom, a halogen atom or a halogenated or non-halogenated alkyl group having 1 to 20 carbon atoms, and Y is oxygen (O), sulfur (S) or NR, where R is H or an organic moiety, subject to the proviso that the halogenated heteroalkyl group is comprised of at least one halogen atom.

5 . The polymer of claim 4 , wherein Y is oxygen (O).

6 . The polymer of claim 4 , wherein the halogenated heteroalkyl group is comprised of at least one fluorine atom.

7 . The polymer of claim 4 , wherein the halogenated heteroalkyl group is comprised of from 2 to 4 carbon atoms.

8 . The polymer of claim 1 , wherein the at least two active hydrogen-containing functional groups are selected from the group consisting of hydroxyl groups, thiol groups, secondary amino groups and primary amino groups.

9 . The polymer of claim 1 , wherein the at least one co-reactant is selected from the group consisting of polyisocyanates, polyisocyanate-functionalized urethane prepolymers, polycarboxylic acids, and epoxy resins.

10 . The polymer of claim 1 , wherein the at least one halogenated reactant corresponds to formula (II):
(R 1 —Y—) x R 2 (YH) y   (II)
wherein R 1 is a halogenated alkyl or halogenated alkenyl group, R 2 is an organic moiety, Y is oxygen (O), sulfur (S) or NR, where R is H or an organic moiety, x is an integer of 1 or more and y is an integer of 2 or more.

11 . The polymer of claim 10 , wherein R 1 comprises at least one fluorine atom.

12 . The polymer of claim 10 , wherein R 1 corresponds to formula (III):
CX 1 X 2 HCX 3 X 4 —  (III)
wherein X 1 , X 2 , X 3 and X 4 are independently selected from a hydrogen atom, a halogen atom or a halogenated or non-halogenated alkyl group having 1 to 20 carbon atoms, provided that at least one of X 1 , X 2 , X 3 or X 4 is halogen or a halogenated alkyl group.

13 . The polymer of claim 10 , wherein x+y is an integer of from 3 to 6.

14 . The polymer of claim 10 , wherein x is 1 and y is 2.

15 . The polymer of claim 10 , wherein Y is oxygen (O).

16 . The polymer of claim 10 , wherein R 2 is a C3-C20 aliphatic moiety.

17 . The polymer of claim 10 , wherein x is 1, y is 2, Y is oxygen (O), and R 2 is a C3-C20 aliphatic moiety.

18 . A method for making a polymer, comprising a step of reacting at least one halogenated reactant comprising at least two active hydrogen-containing functional groups and at least one halogenated heteroalkyl or halogenated heteroalkenyl group and at least one co-reactant comprising at least two functional groups reactive with the active hydrogen groups of the at least one halogenated reactant.

19 . The method of claim 18 , wherein the polymer is a polyamide, polyester, polyurea, polyurethane or epoxy polymer.

20 . The method of claim 18 , wherein the at least one halogenated reactant comprises at least two active hydrogen-containing functional groups and at least one halogenated heteroalkyl group corresponding to formula (I):
CX 1 X 2 HCX 3 X 4 —Y—  (I)
wherein X 1 , X 2 , X 3 and X 4 are independently selected from a hydrogen atom, a halogen atom or a halogenated or non-halogenated alkyl group having 1 to 20 carbon atoms, and Y is oxygen (O), sulfur (S) or NR, where R is H or an organic moiety, subject to the proviso that the halogenated heteroalkyl group is comprised of at least one halogen atom.

21 . An article of manufacture comprising at least one polymer in accordance with claim 1 , wherein the article of manufacture is selected from the group consisting of coatings, paints, adhesives, sealants, fibers, molded articles, films, sheets, composites and laminates.

22 . Use of a polymer in accordance with claim 1 to manufacture an article selected from the group consisting of coatings, paints, adhesives, sealants, fibers, molded articles, films, sheets, composites and laminates.

Assignees

• Arkema Inc

Inventors

• Chen Benjamin Bin
• Polsz Craig A
• Clarkson Lucy

Classifications

• C08G18/3812

  having fluorine atoms · CPC title

• C08G18/3806

  having chlorine and/or bromine atoms · CPC title

• C08G18/3804

  Polyhydroxy compounds · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C08G18/3814 Primary

  Polyamines · CPC title